Highly Convergent Total Synthesis of (+)-Lithospermic Acid via a Late-Stage Intermolecular C-H Olefination

Dong-Hui Wang and Jin-Quan Yu

J. Am. Chem. Soc.,
2011, 133, (15), 5767-5769; 10.1021/ja2010225


A key goal of the CCHF is to develop C–H Functionalization strategies that streamline the synthesis of high value molecules, such as Natural products or therapeutic agents, in a sustainable and facile way. This report from the Yu group provides an excellent example of a success on the way to this goal.

Lithospermic acid, a therapeutic target due to its potential in the treatment of HIV, was identified as a target for synthesis. Employing an ambitious sequence of C–H Functionalizations, using chemistry from both the Yu and Davies groups, the molecular skeletons has been prepared in far fewer steps than previously acheived.

This is an excellent example of one of the central goals of the CCHF, and it is planned that this will be just the first of many molecular motifs that will benefit from C–H Functionalization.

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